2-羟基-N-[4-(三氟甲基)苯基]苯甲酰胺 | 42043-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-N-[4-(三氟甲基)苯基]苯甲酰胺
• 英文名称: N-(4-trifluoromethylphenyl)-2-hydroxy-benzamide
• 英文别名: 2-hydroxy-N-(4-(trifluoromethyl)phenyl)benzamide；2-hydroxy-N-[4-(trifluoromethyl)phenyl]benzamide
• CAS: 42043-15-2
• 化学式: C₁₄H₁₀F₃NO₂
• 分子量: 281.234
• InChiKey: DXZLRIRZSCXNRR-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  302.9±42.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-羟基-N-[4-(三氟甲基)苯基]苯甲酰胺 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Novel ZnII complexes of 2-(2-hydroxyphenyl)benzothiazoles ligands: electroluminescence and application as host materials for phosphorescent organic light-emitting diodes

  摘要：

  设计并合成了一组含有2-羟基苯基苯并噻唑（BTZ）配体的新型锌配合物，其中BTZ配体中苯并噻唑环的6位上连接有不同的取代基（OCH3、CH3、F、CF3、COOCH2CH3）。研究了这些锌配合物的光致发光（PL）和电致发光（EL）行为。通过简单地改变取代基，这些锌配合物的发射颜色很容易从蓝绿色调整为黄色，强吸电子取代基有利于较长波长的荧光。当这些锌络合物用作有机发光二极管（OLED）中的非掺杂发光层时，获得了高效的EL。此外，这些锌配合物被证明能够充当红色磷光OLED中铱磷光体的三重态主体。以本发明的锌配合物为主体、三(2-苯基异喹啉)铱作为掺杂发射极的红色磷光OLED实现了17.5%的高外量子效率，与采用本发明的锌配合物的器件的外量子效率(12.6%)相比大大提高。传统的4,4′-双(N-咔唑基)联苯(CBP)作为主体。本研究成功开发了新型锌配合物作为磷光 OLED 的电子传输主体材料。

  DOI：

  10.1039/c2jm34599d
• 作为产物：
  描述：

  阿司匹林 在 咪唑 、 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-羟基-N-[4-(三氟甲基)苯基]苯甲酰胺
  参考文献：
  名称：

  A New Rational Hypothesis for the Pharmacophore of the Active Metabolite of Leflunomide, a Potent Immunosuppressive Drug

  摘要：

  Leflunomide is one of the most promising disease-modifying antirheumatic drug now in clinical trials for the treatment of rheumatoid arthritis. Metabolic studies have indicated that leflunomide is rapidly processed in vivo to an active metabolite, A771726 (2). To identify the chemical characteristics necessary for the immunosuppressive activity of 2, configurational and conformational studies were carried out on the latter and its inactive analogues (ethyl 3-hydroxy-2-((4-(trifluoromethyl)phenyl)carbamoyl)but-2-enoate 3a, and 3-hydroxy-2-nitro-N(4-(trifluoromethyl)phenyl)but-2 -enamide, 3b). These studies suggested that the pharmacophore responsible for the immunosuppressive activity of 2 is a beta-keto amide with the enolic hydroxy group cis to the amidic moiety. To verify this hypothesis, a new class of immunosuppressive agents was designed and synthesized. Their testing in vitro and in vivo identified compounds which were more potent than both leflunomide and 2 and above all confirmed our hypothesis as to the key structural and chemical determinants for the immunosuppressive properties of 2 and our compounds.

  DOI：

  10.1021/jm970039n

文献信息

• Analogues of the active metabolite of leflunomide
  申请人：Italfarmaco S.p.A.

  公开号：US05905090A1

  公开（公告）日：1999-05-18

  Analogues of the active metabolite of leflunomide, and to the use thereof as immunosuppressive and/or antinflammatory agents.

  乐氟硝咪衍生物的活性代谢物类似物，及其作为免疫抑制剂和/或抗炎剂的使用。
• PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE OF SALICYLANILIDES FOR TREATMENT OF HEPATITIS VIRUSES
  申请人：Semple J. Edward

  公开号：US20120108592A1

  公开（公告）日：2012-05-03

  A new class of salicylanilides is described. These compounds show strong activity against hepatitis viruses.

  描述了一类新的水杨酰苯胺类化合物。这些化合物对肝炎病毒表现出强大的活性。
• Multivariate Regression with Substituent Shift Increments. IV. 2-(4-X-Phenyl)-1,3-dihydro-2H-isoindole-1,3-diones and 3-(4-X-Phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones
  作者：Miroslav Holík、Zdeněk Friedl、Karel Waisser、Jiří Gregor

  DOI：10.1135/cccc19991709

  日期：——

  Two series of para disubstituted benzenes were studied: 2-(4-X-phenyl)-1,3-dihydro- 2H-isoindole-1,3-diones (1) and 3-(4-X-phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones (2). Their ¹H and ¹³C chemical shifts were correlated with substituent shift increments (SSI) a_j and z_j, respectively. For ¹³C chemical shifts, all four z_j values, z_i, z_o, z_m, and z_p, were used to check the assignment and to find out possible variables for improvement of regression equations. Significant deviations from plain additivity were observed in the case of δ_H3 and δ_C3 chemical shifts. This can be explained by changes in diamagnetic anisotropy contribution induced by different twist of 4-substituent from the benzene plane caused by variable substituent in position 1.

  研究了两组para二取代苯：2-(4-X-苯基)-1,3-二氢-2H-异吲哚-1,3-二酮(1)和3-(4-X-苯基)-3,4-二氢-2H-1,3-苯并噁嗪-2,4-二酮(2)。它们的¹H和¹³C化学位移与取代基位移增量(SSl) a_j和z_j相关。对于¹³C化学位移，所有四个z_j值，z_i，z_o，z_m和z_p，都被用来检查分配并找出可能改进回归方程的变量。在δ_H3和δ_C3化学位移的情况下观察到明显的偏离简单加性。这可以通过由位于位置1的可变取代基引起的苯环平面外4-取代基的不同扭曲引起的抗磁性异向贡献的变化来解释。
• Trifluoroacetic Acid-Mediated Denitrogenative <i>ortho</i>-Hydroxylation of 1,2,3-Benzotriazin-4(3<i>H</i>)-ones: A Metal-Free Approach
  作者：Kanagaraj Madasamy、Madasamy Hari Balakrishnan、Ramaraju Korivi、Subramaniyan Mannathan

  DOI：10.1021/acs.joc.2c00354

  日期：2022.7.1

  An efficient trifluoroacetic acid-mediated denitrogenative hydroxylation of 1,2,3-benzotriazin-4(3H)-ones is described. This metal-free approach is compatible with a wide range of 1,2,3-benzotriazin-4(3H)-ones, affording ortho-hydroxylated benzamides in good to high yields with a short reaction time. The reaction is believed to proceed via a benzene diazonium intermediate. The synthetic utility of

  描述了一种有效的三氟乙酸介导的 1,2,3-benzotriazin-4(3 H )-ones 的脱氮羟基化。这种不含金属的方法与多种 1,2,3-benzotriazin-4(3 H )-one相容，可在较短的反应时间内以良好至高产率提供邻羟基化苯甲酰胺。据信该反应通过苯重氮中间体进行。该反应的合成效用通过以良好收率制备抗微生物药物利肝素 C 和苯并恶嗪-2,4(3 H )-二酮类化合物得到成功证明。
• Inhibition by 3-deoxyflavonoids of T-lymphocyte activation and therapies related thereto
  申请人：——

  公开号：US20040102386A1

  公开（公告）日：2004-05-27

  3-Deoxyflavonoid compounds and methods for inhibiting T-cell activity and treating diseases and disorders (e.g., autoimmune disorders, inflammatory disorders, diabetes, ALS, MS, rheumatoid arthritis, etc.). In some cases the efficacy and/or duration of action of luteolin and/or other 3-deoxyflavonoid compounds may be increased by administering such compounds along with Rutin, a Rutin congener and/or a Rutin derivative. Also, in some cases, first pass metabolism of luteolin or other 3-deoxyflavonoids may be avoided by administering such compounds by parenteral routes (e.g., routes wherein absorption occurs at sites other than the stomach or intestinal mucosa, such as sublingual, buccal, intranasal, injection, etc.).

  3-去氧黄酮类化合物和用于抑制T细胞活性和治疗疾病和障碍（例如自身免疫性疾病、炎症性疾病、糖尿病、肌萎缩侧索硬化症、多发性硬化症、类风湿性关节炎等）的方法。在某些情况下，通过与芦丁、芦丁同系物和/或芦丁衍生物一起给予这些化合物，可以增加槲皮素和/或其他3-去氧黄酮类化合物的功效和/或作用持续时间。此外，在某些情况下，通过经肠外途径（例如舌下、颊黏膜、鼻内、注射等吸收发生在胃或肠粘膜以外的部位的途径）给予这些化合物，可以避免槲皮素或其他3-去氧黄酮类化合物的首过代谢。